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About the Role
SysAid is seeking a VP of Sales, Customer Success & Growth to lead its North American go-to-market organization, overseeing new business, retention, and expansion. This role is accountable for the health, forecast, and growth of the entire North American book of business, managing a team of approximately 25 professionals.
Responsibilities
- Own the P&L for North America across new logo acquisition, customer success, and expansion.
- Hire, coach, and manage a team of Senior Directors.
- Build and maintain an accurate, defensible forecast, running consistent pipeline and forecast cadences.
- Partner with the Senior Director of Sales to drive net-new logo growth.
- Own gross revenue retention outcomes, focusing on proactive risk scoring and churn mitigation.
- Drive net revenue expansion by leading upsell, cross-sell, and account growth motions.
- Design and evolve the North American operating model, including territory segmentation, quota setting, and compensation design.
- Represent North American performance, retention metrics, and growth strategy to executive leadership and the board.
Requirements
- 10+ years of progressive GTM leadership experience with direct P&L ownership across sales, customer success, and/or expansion, ideally in B2B SaaS or enterprise software.
- Proven experience managing Senior Directors or equivalent leaders.
- A strong track record of expanding pipeline coverage, improving win rates, growing average deal size, and shortening sales cycles.
- Demonstrated success driving retention, reducing churn, and growing expansion revenue within an existing customer base.
- Deep experience building or running risk-scoring processes that leadership and the board can rely on.
- Experience presenting commercial performance and growth metrics to executive leadership and boards.
- Prior experience in cybersecurity, ITSM, or adjacent enterprise IT software is a plus.
Skills
- Generative AI
- Conversational AI
- IT Service Management (ITSM)
- Sales leadership
- Customer Success leadership
- Growth leadership
- Pipeline management
- Forecasting
- P&L management
- Team management
- Strategic planning
- Operational design
Location
- Toronto, Ontario, Canada
Work Type
- Hybrid
Experience Level
- VP level
- 10+ years of GTM leadership experience
Salary/Compensations
- OTE (70% Base Salary, 30% Commission)
Benefits
- Stock options
- Matched RRSP
- Health & Dental Plan coverage
- Quarterly engagement events
- Summer party
- Holiday party
About the Company
- SysAid is a dynamic SaaS company specializing in IT Service Management while pioneering generative and conversational AI.
- Recognized as a leading innovator in the industry, featured in the Gartner Magic Quadrant for ITSM and honored with AWS's Rising ISV Star Award.
- With over 4,000 clients across 140 countries and a daily impact on over 9 million end-users, SysAid is committed to transforming the ITSM landscape.
Equal Opportunity
- SysAid is an equal opportunity employer.
- We celebrate diversity and are committed to creating an inclusive environment for all employees.